How to Improve Your Strategic Thinking Muscle

Lessons from Witkins and three women who shaped my thinking

August has been a month of celebration for women, and I have been reflecting on the three incredibly smart women I have been privileged to work under across my career. Their way of thinking rubbed off on me, and when I problem-solve business issues today, I sometimes catch myself approaching a problem the way one of them would have. Working under them is where I watched strategic thinking up close, and it left me with a question I keep returning to: is strategic thinking nature or nurture?

The honest answer is both. You don’t become a marathon champion without the right physiology, the muscles, the lungs, but even with that endowment, you still have to train very hard. Strategic thinking works the same way. Some people are naturally better at it than others. But if you can’t do anything about your endowment, you focus on the improvement, because the research shows you can get much better with the right training.

Strategic thinking has always been a critical skill at the top of organisations. If you aspire to lead, you must be able to recognise emerging challenges and opportunities, establish the right priorities to focus the organisation, and mobilise people to adapt to change, both internal and external.

In The Six Disciplines of Strategic Thinking, Michael Watkins identifies six disciplines that sit beneath this ability, and every one of them is trainable for anyone keen.

1. Pattern recognition

This is the foundational discipline of strategic thinking: the ability to find the signal, the important information, in a sea of noise. It is not just absorbing what is happening, but asking why it is happening and connecting the dots. When grandmasters look at a chessboard, they don’t see pieces in isolation; they see concentrations of power, opportunities, and vulnerabilities in the configuration. This same pattern recognition is important in studying organisations and diagnosing why things are the way they are.

2. Systems analysis

At the heart of your ability as a leader to navigate complexity, you need the discipline of systems analysis. This is a core mental discipline required to manage complexity, build functional mental models, and predict the ripple effects of business decisions.

You need to learn to simplify complexities by breaking down complicated, chaotic environments or organisations into essential component elements and understand how they interact. This allows leaders to construct simplified mental maps of a domain so they can anticipate that changing one variable (like product pricing or sales incentives) will create downstream reactions and feedback loops elsewhere in the organisation.

3. Mental agility

Watkins calls this level-shifting: cloud-to-ground thinking. It is the ability to sit at a high level and see the big picture of what’s going on, but also to drill down into the detail when necessary. Great strategic thinkers move between these levels of analysis fluidly and intentionally.

Claire, the Head of Anthropology I worked under at Demographica, did this better than anyone I have met. She would come at a problem through anthropological lenses no one had thought of, then drop into the detail of the research and land on strategic insights that reframed both the findings and our recommendations to the client, insights I, looking at the same material, had simply not seen.

4. Structured problem-solving

This is what strategic thinkers do with teams: a rigorous process for framing the right problem, generating and testing the right options, and moving stakeholders towards alignment about the way forward. I watched Evelien, then Head of Customer Insights at Yoco, run this discipline exceptionally well, and it shaped how I work today.

I now use it in our monthly management reports. We used to run a fragmented model in which marketing, sales, finance, support, and dev each reported independently, which hid problems rather than surfacing them. I introduced a single spreadsheet that captures every department’s activity for the month. The cross-departmental chains became visible immediately: a wrongly targeted marketing campaign brought in the wrong leads, sales wasted time on prospects who were never going to qualify, the clients who did convert didn’t stay long, retention dropped, and finance took the hit.

Support calls spiked with requests for features that didn’t exist.

When every team can see how its actions affect the others, you stop treating symptoms in one department and start solving causes across the business.

5. Visioning

Visioning defines the future state you are trying to build and gives teams a compelling reason to care. The core tension is between ambition and achievability. Err too far towards ambition, and people won’t believe it can be done; err too far towards achievability, and it excites no one. Both extremes demotivate, which is exactly what a vision exists to prevent.

6. Political savvy

Politics is part of every human organisation; there is no avoiding it. One classic tactic is sequencing: being thoughtful about the order in which you seek buy-in. Say you need Edward on board first, then Paul, with those two behind you, winning over Trevor becomes much easier. But be careful not to overplay your hand in a way that makes Michelle feel threatened, or she may mobilise opposition. Sequencing moves people step by step to a place they would never have gone in a single leap.

Johanna, Chief of Staff and Strategy Executive at Wetility, had this ability. She knew how to mobilise different stakeholders towards a decision, and she did it so well that it was hard to spot sequencing at play.

Watkins can give you the syllabus, but nobody becomes a strategic thinker by reading about the six disciplines, the same way nobody runs a marathon by studying training plans.

I built the muscle I have by watching these women think, so as Women’s Month closes, here is a different kind of homework: find the sharpest strategic thinker you can get close to, and study how they think, not just what they decide.

The disciplines give you the vocabulary. The people around you are the gym.